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2-Isopropylmaleic acid (YMDB00442)

Identification
YMDB IDYMDB00442
Name2-Isopropylmaleic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionIsopropylmaleic acid, also known as 2-isopropylmaleate, belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present. Based on a literature review a small amount of articles have been published on Isopropylmaleic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Isopropylmaleate
  • 2-isopropylmaleic acid
  • beta-Isopropylmaleate
  • b-Isopropylmaleate
  • b-Isopropylmaleic acid
  • beta-Isopropylmaleic acid
  • Β-isopropylmaleate
  • Β-isopropylmaleic acid
  • Isopropylmaleate
  • Isopropylmaleic acid
  • (2Z)-2-(1-Methylethyl)-2-butenedioic acid
CAS numberNot Available
WeightAverage: 158.1519
Monoisotopic: 158.057908808
InChI KeyNJMGRJLQRLFQQX-HYXAFXHYSA-N
InChIInChI=1S/C7H10O4/c1-4(2)5(7(10)11)3-6(8)9/h3-4H,1-2H3,(H,8,9)(H,10,11)/b5-3-
IUPAC Name(2Z)-2-(propan-2-yl)but-2-enedioic acid
Traditional IUPAC Name2-isopropylmaleic acid
Chemical FormulaC7H10O4
SMILESCC(C)C(=C\C(O)=O)\C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.64 g/LALOGPS
logP1.05ALOGPS
logP1.09ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.11 m³·mol⁻¹ChemAxon
Polarizability15.11 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Leucine BiosynthesisPW002475 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Valine, leucine and isoleucine biosynthesisec00290 Map00290
SMPDB Reactions
2-Isopropylmalic acid → water + 2-Isopropylmaleic acid
2-Isopropylmaleic acid + water → 3-Isopropylmalate
KEGG Reactions
water + 2-Isopropylmaleic acid ↔ 2-Isopropylmalic acid
3-Isopropylmalate ↔ water + 2-Isopropylmaleic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ox-9800000000-c1dc75af0432077c0384JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dr-9470000000-5b930a576d9e4924347aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-45d74194c5fbfea04a10JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-7900000000-7e85e22040474be6339cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-9100000000-672bc73595a1f6b84201JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-1900000000-48b9e2f85f15343470aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-090a-5900000000-5c4991c8530e2f8a6edaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kb-9400000000-0d37fa6e2313dc5f09a3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ow-6900000000-9e65c798b41317f5b6e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-9200000000-6dfbad4c912b766f9b7eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-74dbf533069b6e671b6cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-9800000000-698f88590edad48bf4c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-9400000000-d1228db2dbcd7906ae8aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-9000000000-a5bd12b0d9ab424964ccJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Suzuki, T., Tamura, S., Nakanishi, H., Tashiro, M., Nishizawa, N. K., Yoshimura, E. (2007). "Reduction of aluminum toxicity by 2-isopropylmalic acid in the budding yeast Saccharomyces cerevisiae." Biol Trace Elem Res 120:257-263.17916978
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17275
HMDB IDHMDB0012241
Pubchem Compound ID21954611
Kegg IDC02631
ChemSpider ID4444164
FOODB IDFDB028883
Wikipedia IDIsopropylmalic_acid
BioCyc IDNot Available

Enzymes

Protein Details
1. 3-isopropylmalate dehydratase
General function:
Involved in 3-isopropylmalate dehydratase activity
Specific function:
Catalyzes the isomerization between 2-isopropylmalate and 3-isopropylmalate, via the formation of 2-isopropylmaleate
Gene Name:
LEU1
Uniprot ID:
P07264
Molecular weight:
85793.70313
Reactions
(2R,3S)-3-isopropylmalate → (2S)-2-isopropylmaleate + H(2)O.
(2S)-2-isopropylmaleate + H(2)O → (2S)-2-isopropylmalate.